Hydrochloric Acid → N-Methyl-2 methylamino-alpha-(3-methyl-2-thienyl)-benzeneethanamine dihydrochloride

HRID 1721332Notes

Reaction equation

HRID 1721332 reaction equation
[CH:1]([N:3](C)[CH:4]([C:14]1[S:15][CH:16]=[CH:17][C:18]=1[CH3:19])[CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[NH:12][CH3:13])=O.[ClH:21]>C(OCC)C.CO>[ClH:21].[ClH:21].[CH3:1][NH:3][CH:4]([C:14]1[S:15][CH:16]=[CH:17][C:18]=1[CH3:19])[CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[NH:12][CH3:13]

Participants

5

Reactant 2

HCID 313Hydrochloric Acid2×HCID 11778875N-formyl-N-methyl-2-methylamino-alpha-(3-methyl-2-thienyl)benzeneethanamine

Product 1

HCID 22414479N-Methyl-2 methylamino-alpha-(3-methyl-2-thienyl)-benzeneethanamine dihydrochloride

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 3283Diethyl EtherSolvent

Procedure

N-Formyl-N-methyl-2-methylamino-α-(3-methyl-2-thienyl)benzenethanamine (4.1 g) was treated with 18 ml of 3N hydrochloric acid. After refluxing for 1.5 hours the solution was decanted over ice, basified with 12 ml of a 50% aqueous sodium hydroxide solution and extracted with dichloromethane (3×60 ml). The organic phase was dried over anhydrous sodium sulfate and concentrated to an oil. Purification of the oil was accomplished by HPLC (Water's Associates Prep LC/System 500, silica gel, elution with methanol). Concentration of the appropriate fractions afforded a residue which was dissolved in diethyl ether, filtered free of insolubles, and concentrated to afford N-methyl-2-methylamino-α-(3-methyl-2-thienyl)benzeneeethanamine as an oil. The oil was dissolved in methanol and treated with ethereal hydrogen chloride. Dilution with diethyl ether precipitated 2.4 g of the corresponding dihydrochoride salt, mp 191°-192° C.

Workup

  1. temperatureAfter refluxing for 1.5 hours the solution
  2. customwas decanted over ice
  3. extractionextracted with dichloromethane (3×60 ml)
  4. dry with materialThe organic phase was dried over anhydrous sodium sulfate
  5. concentrationconcentrated to an oil
  6. customPurification of the oil
  7. washwas accomplished by HPLC (Water's Associates Prep LC/System 500, silica gel, elution with methanol)
  8. customConcentration of the appropriate fractions afforded a residue which
  9. filtrationfiltered free of insolubles
  10. concentrationconcentrated
  11. customto afford N-methyl-2-methylamino-α-(3-methyl-2-thienyl)benzeneeethanamine as an oil
  12. customDilution with diethyl ether precipitated 2.4 g of the corresponding dihydrochoride salt, mp 191°-192° C.

Sources & evidence

ORD record
ord-2d6c7274644240fea6bb0c68693c648d
Source dataset
uspto-grants-1996_04
Patent number
US05510346

Reaction notes

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